tert-Butyldimethylsilanol → HCID 12106183, compound

HRID 2362492Notes

Reaction equation

HRID 2362492 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][C:15]=1[N+:24]([O-])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Si](C)(C)O)(C)(C)C.[H][H]>C1(C)C=CC=CC=1.[Pt]>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][C:15]=1[NH2:24])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 554527tert-ButyldimethylsilanolHCID 12106182HCID 12106182, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 12106183HCID 12106183, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

The mixture of [4-(tert-butyldimethylsilanyloxy)butyl](3-nitro-quinolin-4-yl)amine and tert-butyldimethylsilanol (110 g) from the previous step was dissolved in toluene (880 mL) and placed in a Parr hydrogenation vessel along with 5% platinum on carbon catalyst (3.0 g). The vessel was pressurized to 50 psi (3.4×105 Pa) hydrogen and shaken on the Parr apparatus for 1.5 hours, occasionally adding additional hydrogen to maintain a pressure of 50 psi (3.4×105 Pa). After 3 hours, the reaction mixture was filtered through CELITE filter agent and concentrated under reduced pressure to provide N4-[4-(tert-butyldimethylsilanyloxy)butyl]quinoline-3,4-diamine as a dark oil that was used directly in the next step without further purification.

Workup

  1. temperatureto maintain a pressure of 50 psi (3.4×105 Pa)
  2. waitAfter 3 hours
  3. filtrationthe reaction mixture was filtered through CELITE
  4. filtrationfilter agent
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f50b14ad11f74270b3b21775f4b46177
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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